JP2018052972A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2018052972A5 JP2018052972A5 JP2017234081A JP2017234081A JP2018052972A5 JP 2018052972 A5 JP2018052972 A5 JP 2018052972A5 JP 2017234081 A JP2017234081 A JP 2017234081A JP 2017234081 A JP2017234081 A JP 2017234081A JP 2018052972 A5 JP2018052972 A5 JP 2018052972A5
- Authority
- JP
- Japan
- Prior art keywords
- labeling reagent
- compound
- amino
- mass spectrometry
- reagent according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000002372 labelling Methods 0.000 claims description 39
- 239000003153 chemical reaction reagent Substances 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 238000004949 mass spectrometry Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 8
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 7
- 150000001717 carbocyclic compounds Chemical group 0.000 claims description 6
- 238000004885 tandem mass spectrometry Methods 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 102000004169 proteins and genes Human genes 0.000 claims description 4
- 108090000623 proteins and genes Proteins 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 238000005259 measurement Methods 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 238000002541 precursor ion scan Methods 0.000 claims description 2
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims description 2
- 238000002553 single reaction monitoring Methods 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- -1 carbamate compound Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 125000005208 trialkylammonium group Chemical group 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001601 aromatic carbocyclic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000005412 pyrazyl group Chemical group 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002036446 | 2002-02-14 | ||
| JP2002036446 | 2002-02-14 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015188056A Division JP6278210B2 (ja) | 2002-02-14 | 2015-09-25 | アミノ官能性化合物の分析方法及び分析試薬 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020008872A Division JP7055267B2 (ja) | 2002-02-14 | 2020-01-23 | アミノ官能性化合物の分析方法及び分析試薬 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018052972A JP2018052972A (ja) | 2018-04-05 |
| JP2018052972A5 true JP2018052972A5 (enExample) | 2018-06-07 |
| JP6699645B2 JP6699645B2 (ja) | 2020-05-27 |
Family
ID=27678084
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003568398A Expired - Lifetime JP4453363B2 (ja) | 2002-02-14 | 2003-02-13 | アミノ官能性化合物の分析方法及び分析試薬 |
| JP2009269796A Expired - Lifetime JP5136542B2 (ja) | 2002-02-14 | 2009-11-27 | アミノ官能性化合物の分析方法及び分析試薬 |
| JP2012216013A Expired - Lifetime JP5842775B2 (ja) | 2002-02-14 | 2012-09-28 | アミノ官能性化合物の分析方法及び分析試薬 |
| JP2015188056A Expired - Lifetime JP6278210B2 (ja) | 2002-02-14 | 2015-09-25 | アミノ官能性化合物の分析方法及び分析試薬 |
| JP2017234081A Expired - Lifetime JP6699645B2 (ja) | 2002-02-14 | 2017-12-06 | アミノ官能性化合物の分析方法及び分析試薬 |
| JP2020008872A Expired - Lifetime JP7055267B2 (ja) | 2002-02-14 | 2020-01-23 | アミノ官能性化合物の分析方法及び分析試薬 |
Family Applications Before (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003568398A Expired - Lifetime JP4453363B2 (ja) | 2002-02-14 | 2003-02-13 | アミノ官能性化合物の分析方法及び分析試薬 |
| JP2009269796A Expired - Lifetime JP5136542B2 (ja) | 2002-02-14 | 2009-11-27 | アミノ官能性化合物の分析方法及び分析試薬 |
| JP2012216013A Expired - Lifetime JP5842775B2 (ja) | 2002-02-14 | 2012-09-28 | アミノ官能性化合物の分析方法及び分析試薬 |
| JP2015188056A Expired - Lifetime JP6278210B2 (ja) | 2002-02-14 | 2015-09-25 | アミノ官能性化合物の分析方法及び分析試薬 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020008872A Expired - Lifetime JP7055267B2 (ja) | 2002-02-14 | 2020-01-23 | アミノ官能性化合物の分析方法及び分析試薬 |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US7148069B2 (enExample) |
| EP (3) | EP2336763A1 (enExample) |
| JP (6) | JP4453363B2 (enExample) |
| AU (1) | AU2003211941A1 (enExample) |
| CA (1) | CA2475011C (enExample) |
| WO (1) | WO2003069328A1 (enExample) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2336763A1 (en) * | 2002-02-14 | 2011-06-22 | Ajinomoto Co., Inc. | Method for analysis of compounds with amino group and analytical reagent thereof |
| US20050014279A1 (en) * | 2003-07-14 | 2005-01-20 | Nguyen Hoa Duc | Method of analysis of amine by mass spectrometry |
| WO2005050188A1 (ja) * | 2003-11-21 | 2005-06-02 | Eisai Co., Ltd. | 同位体標識化内部標準物質を用いる定量方法、該定量方法を実行する解析システムおよび該解析のためのプログラム |
| US20080206737A1 (en) * | 2004-05-19 | 2008-08-28 | Hunter Christie L | Expression quantification using mass spectrometry |
| US20070054345A1 (en) * | 2004-05-19 | 2007-03-08 | Hunter Christie L | Expression quantification using mass spectrometry |
| EP1750126B1 (en) | 2004-05-26 | 2015-09-16 | Ajinomoto Co., Inc. | Method and apparatus for analyzing aminofunctional compound |
| US20070048752A1 (en) | 2004-07-12 | 2007-03-01 | Applera Corporation | Mass tags for quantitative analyses |
| US20060172319A1 (en) * | 2004-07-12 | 2006-08-03 | Applera Corporation | Mass tags for quantitative analyses |
| US8969089B2 (en) | 2004-10-12 | 2015-03-03 | Quest Diagnostics Investments, Inc. | Analysis of amino acids in body fluid by liquid chromatography-mass spectrometry |
| US20060183238A1 (en) | 2005-02-09 | 2006-08-17 | Applera Corporation | Amine-containing compound analysis methods |
| JP2007163423A (ja) * | 2005-12-16 | 2007-06-28 | Ajinomoto Co Inc | 質量分析計によるアミノ酸分析方法 |
| JP4771297B2 (ja) * | 2006-02-08 | 2011-09-14 | 日本電気株式会社 | ペプチドの修飾方法及びペプチドの同定方法 |
| EP1983346A4 (en) * | 2006-02-08 | 2010-03-17 | Nec Corp | METHOD FOR CLEAVING A PEPTIDE BOND AT THE C-TERMINAL END OF A PEPTIDE, AND A METHOD FOR DETERMINING THE C-TERMINAL END-ACE AMINO ACID SEQUENCE OF A PEPTIDE |
| EP3543691A1 (en) * | 2007-06-29 | 2019-09-25 | Quest Diagnostics Investments Incorporated | Analysis of amino acids in body fluid by liquid chromatography-mass spectrometry |
| US12367163B2 (en) | 2007-06-29 | 2025-07-22 | Quest Diagnostics Investments Llc | Analysis of amino acids in body fluid by liquid chromatography—mass spectrometry |
| EP2209001A4 (en) | 2007-10-25 | 2010-10-27 | Ajinomoto Kk | METHOD FOR ASSESSING STROKEN GLUCOSE TOLERANCE |
| JP2011504596A (ja) * | 2007-11-26 | 2011-02-10 | ウオーターズ・テクノロジーズ・コーポレイシヨン | サンプル中の分析物を定量測定する際に使用するための内部標準および方法 |
| DK2252584T3 (en) | 2008-02-04 | 2017-01-16 | Prozyme Inc | COMPOUNDS AND PROCEDURES FOR QUICK LABELING OF N-GLYCANS |
| DE102009060102A1 (de) * | 2009-12-21 | 2011-06-22 | Martin-Luther-Universität Halle-Wittenberg, 06108 | Derivatisierungsreagenzien zur tandem-massenspektrometrischen Quantifizierung von Proteinen |
| KR101968485B1 (ko) | 2011-07-21 | 2019-04-12 | 후지필름 와코 준야꾸 가부시키가이샤 | 혈장중 아미노산 분석용 표준액 |
| US10436790B2 (en) | 2011-09-28 | 2019-10-08 | Waters Technologies Corporation | Rapid fluorescence tagging of glycans and other biomolecules with enhanced MS signals |
| CN108947885A (zh) | 2011-09-28 | 2018-12-07 | 沃特世科技公司 | 具有增强的ms信号的聚糖和其它生物分子的快速荧光标记 |
| US11352325B2 (en) | 2011-09-28 | 2022-06-07 | Waters Technologies Corporation | Rapid fluorescence tagging of glycans and other biomolecules with enhanced MS signals |
| WO2013078222A1 (en) | 2011-11-23 | 2013-05-30 | Quest Diagnostics Investments Incorporated | Kisspeptin-54 detection by tandem mass spectrometry |
| KR101824937B1 (ko) | 2012-11-27 | 2018-02-02 | 아지노모토 가부시키가이샤 | 췌장암의 평가 방법, 췌장암 평가 장치, 췌장암 평가 방법, 췌장암 평가 프로그램, 췌장암 평가 시스템 및 정보 통신 단말 장치 |
| JP7055634B2 (ja) | 2014-10-30 | 2022-04-18 | ウオーターズ・テクノロジーズ・コーポレイシヨン | 標識化グリコシルアミンの迅速調製およびそれを生成するグリコシル化生体分子の分析方法 |
| US10502720B2 (en) | 2014-11-13 | 2019-12-10 | Waters Technologies Corporation | Methods for liquid chromatography calibration for rapid labeled N-glycans |
| KR101627841B1 (ko) * | 2015-05-27 | 2016-06-07 | 다이아텍코리아 주식회사 | 싸이오크로멘 타입 화합물 및 그 용도 |
| HUE059723T2 (hu) | 2015-05-29 | 2022-12-28 | Agilent Technologies Inc | Amintartalmú vegyületek jelölésére szolgáló vegyületek és felhasználásuk |
| CN105548432A (zh) * | 2015-12-18 | 2016-05-04 | 乐普药业股份有限公司 | 一种比伐卢定中氨基酸的检测分析方法 |
| EP4559924A3 (en) | 2016-04-24 | 2025-08-06 | Waters Technologies Corporation | Isolation of glycans modified with amphipathic, strongly basic moieties, using charged surface reversed phase chromatopgraphic materials |
| US11061023B2 (en) | 2016-06-21 | 2021-07-13 | Waters Technologies Corporation | Fluorescence tagging of glycans and other biomolecules through reductive amination for enhanced MS signals |
| WO2017222955A1 (en) | 2016-06-21 | 2017-12-28 | Waters Technologies Corporation | Methods of electrospray ionization of glycans modified with amphipathic, strongly basic moieties |
| ES2991049T3 (es) | 2016-06-30 | 2024-12-02 | Ajinomoto Kk | Método para evaluar la cetosis posparto |
| EP3479103B1 (en) | 2016-07-01 | 2022-04-20 | Waters Technologies Corporation | Methods for the rapid preparation of labeled glycosylamines from complex matrices using molecular weight cut off filtration and on-filter deglycosylation |
| US20180094293A1 (en) | 2016-10-03 | 2018-04-05 | Waters Technologies Corporation | Labeled glycan amino acid complexes useful in lc-ms analysis and methods of making the same |
| EP3692372B1 (en) * | 2017-09-08 | 2024-04-17 | F. Hoffmann-La Roche AG | Sulfoxide-based reagent for mass spectrometry |
| EP3732959A4 (en) | 2017-12-28 | 2022-03-30 | Ajinomoto Co., Inc. | POWER CONTROL SYSTEM AND METHOD OF POWER CONTROL |
| JP7424297B2 (ja) | 2018-09-26 | 2024-01-30 | 味の素株式会社 | 取得方法、算出方法、評価装置、算出装置、評価プログラム、算出プログラム、記録媒体、評価システム |
| CN116773710A (zh) * | 2021-07-13 | 2023-09-19 | 清华大学 | 一种覆盖多种代谢物的代谢组和代谢流的试剂盒和使用方法 |
| CN114354801B (zh) * | 2021-12-31 | 2023-07-18 | 山东大学 | （R）-3-Boc-氨基哌啶中三种氨基吡啶异构体含量的分析方法 |
| CN115925614B (zh) * | 2022-12-02 | 2024-03-08 | 中山大学 | 用于发现可与醛基反应的活性物质的小分子探针 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4003912A (en) * | 1973-06-11 | 1977-01-18 | Monsanto Company | Dicarboximido-N-phenylsubstituted carbamates and derivatives |
| JPS5855754A (ja) | 1981-09-30 | 1983-04-02 | Hitachi Ltd | アミノ酸分析方法 |
| JPS6444848A (en) | 1987-08-14 | 1989-02-17 | Hitachi Ltd | Analysis of amino acid |
| US5296599A (en) * | 1991-09-19 | 1994-03-22 | Millipore Corporation | Activated carbamates compounds |
| WO1996002003A1 (en) * | 1994-07-08 | 1996-01-25 | City Of Hope | N-terminal protein sequencing reagents and methods which form amino acid derivatives |
| JP3346965B2 (ja) | 1995-09-14 | 2002-11-18 | 株式会社日立製作所 | アミノ酸分析装置 |
| TW358097B (en) * | 1996-05-24 | 1999-05-11 | Hoffmann La Roche | Beta-lactams and their process and pharmaceutical compositions |
| JP4085443B2 (ja) | 1997-05-07 | 2008-05-14 | 株式会社島津製作所 | アミノ酸の分析試薬及びアミノ酸の分析方法 |
| US6379971B1 (en) * | 1998-02-24 | 2002-04-30 | Target Discovery, Inc. | Methods for sequencing proteins |
| AU755334C (en) * | 1998-08-25 | 2004-02-26 | University Of Washington | Rapid quantitative analysis of proteins or protein function in complex mixtures |
| GB9821393D0 (en) | 1998-10-01 | 1998-11-25 | Brax Genomics Ltd | Protein profiling 2 |
| US6629040B1 (en) * | 1999-03-19 | 2003-09-30 | University Of Washington | Isotope distribution encoded tags for protein identification |
| US6677114B1 (en) * | 1999-04-20 | 2004-01-13 | Target Discovery, Inc. | Polypeptide fingerprinting methods and bioinformatics database system |
| JP4505905B2 (ja) | 1999-11-22 | 2010-07-21 | 住友化学株式会社 | ペプチドのアミノ酸配列決定方法 |
| JP3341041B2 (ja) * | 2000-02-23 | 2002-11-05 | 独立行政法人産業技術総合研究所 | ペプチドのアミノ酸配列解析方法 |
| AUPQ664300A0 (en) * | 2000-04-03 | 2000-05-04 | Proteome Systems Ltd | Macromolecule detection |
| US6716634B1 (en) * | 2000-05-31 | 2004-04-06 | Agilent Technologies, Inc. | Increasing ionization efficiency in mass spectrometry |
| WO2002004936A1 (fr) * | 2000-07-11 | 2002-01-17 | Japan Science And Technology Corporation | Sonde pour spectrometrie de masse d'un echantillon liquide |
| US20060141632A1 (en) | 2000-07-25 | 2006-06-29 | The Procter & Gamble Co. | New methods and kits for sequencing polypeptides |
| JP3508710B2 (ja) | 2000-09-01 | 2004-03-22 | 株式会社日立製作所 | アミノ酸分析方法および装置 |
| CA2426731A1 (en) * | 2000-10-23 | 2002-06-20 | Genetics Institute, Llc. | Acid-labile isotope-coded extractant (alice) and its use in quantitative mass spectrometric analysis of protein mixtures |
| WO2002046770A2 (en) * | 2000-10-23 | 2002-06-13 | Genetics Institute, Llc | Isotope-coded ionization-enhancing reagents (icier) for high-throughput protein identification and quantitation using matrix-assisted laser desorption ionization mass spectrometry |
| US20030045552A1 (en) * | 2000-12-27 | 2003-03-06 | Robarge Michael J. | Isoindole-imide compounds, compositions, and uses thereof |
| US6818454B2 (en) * | 2001-02-16 | 2004-11-16 | Battelle Memorial Institute | Phosphoprotein binding agents and methods of their use |
| JP3464665B2 (ja) | 2002-01-07 | 2003-11-10 | 株式会社日立製作所 | アミノ酸分析装置 |
| EP2336763A1 (en) * | 2002-02-14 | 2011-06-22 | Ajinomoto Co., Inc. | Method for analysis of compounds with amino group and analytical reagent thereof |
| EP1750126B1 (en) * | 2004-05-26 | 2015-09-16 | Ajinomoto Co., Inc. | Method and apparatus for analyzing aminofunctional compound |
-
2003
- 2003-02-13 EP EP10012964A patent/EP2336763A1/en not_active Withdrawn
- 2003-02-13 EP EP10012963.4A patent/EP2317307B1/en not_active Expired - Lifetime
- 2003-02-13 JP JP2003568398A patent/JP4453363B2/ja not_active Expired - Lifetime
- 2003-02-13 WO PCT/JP2003/001463 patent/WO2003069328A1/ja not_active Ceased
- 2003-02-13 AU AU2003211941A patent/AU2003211941A1/en not_active Abandoned
- 2003-02-13 CA CA2475011A patent/CA2475011C/en not_active Expired - Lifetime
- 2003-02-13 EP EP03705088.7A patent/EP1475632B1/en not_active Expired - Lifetime
-
2004
- 2004-08-16 US US10/918,380 patent/US7148069B2/en not_active Expired - Lifetime
-
2006
- 2006-09-01 US US11/514,130 patent/US9274123B2/en not_active Expired - Fee Related
-
2009
- 2009-11-27 JP JP2009269796A patent/JP5136542B2/ja not_active Expired - Lifetime
-
2012
- 2012-09-28 JP JP2012216013A patent/JP5842775B2/ja not_active Expired - Lifetime
-
2015
- 2015-09-25 JP JP2015188056A patent/JP6278210B2/ja not_active Expired - Lifetime
-
2016
- 2016-01-21 US US15/003,235 patent/US9658234B2/en not_active Expired - Lifetime
-
2017
- 2017-12-06 JP JP2017234081A patent/JP6699645B2/ja not_active Expired - Lifetime
-
2020
- 2020-01-23 JP JP2020008872A patent/JP7055267B2/ja not_active Expired - Lifetime
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2018052972A5 (enExample) | ||
| JP2013015537A5 (enExample) | ||
| JP7055267B2 (ja) | アミノ官能性化合物の分析方法及び分析試薬 | |
| CN105102682B (zh) | 苯胺类化合物的电化学偶合 | |
| JP2010071995A5 (enExample) | ||
| Sharma et al. | (Bis) urea and (bis) thiourea inhibitors of lysine-specific demethylase 1 as epigenetic modulators | |
| US10336713B2 (en) | Triazole-based reader molecules and methods for synthesizing and use thereof | |
| Chen et al. | Iodine mediated deprotection of N-tert-butanesulfinyl amines: a functional group compatible method | |
| JP2015524058A5 (enExample) | ||
| JP2018538511A5 (enExample) | ||
| Seybold | Quantum Chemical‐QSPR Estimation of the Acidities and Basicities of Organic Compounds | |
| Solís-Calero et al. | DFT study of the mechanism of the reaction of aminoguanidine with methylglyoxal | |
| Duca et al. | Understanding the chemical reactivity of dihydroxyfumaric acid and its derivatives through conceptual DFT | |
| JP2017088530A (ja) | ホスホリルコリン修飾アミド化合物の製造方法 | |
| RU2005131004A (ru) | Способ оределения молекулярной массы соединения, содержащего моноэфир фосфорной кислоты, и добавка для масс-спектрометрии | |
| Elrod | A comprehensive computational investigation of the enthalpies of formation and proton affinities of C4H7N and C3H3ON compounds | |
| JP2013523646A5 (enExample) | ||
| CY1118348T1 (el) | Μεθοδος παρασκευης μεταξαλονης | |
| Franco-Pérez et al. | A new tricomponent reaction for the synthesis of symmetric and asymmetric alkyl bisphosphoramidates | |
| JP2011101862A5 (enExample) | ||
| RU2560180C1 (ru) | N'-(1-метилэтилиден)гептадекафтороктилкарбоксамидразон в качестве стандартного образца состава для количественного определения фтора в органических соединениях спектрофотометрическим методом, способ его получения и промежуточное соединение | |
| JP2006526645A5 (enExample) | ||
| Machado et al. | 1-(7-Chloro-1, 4-dihydroquinolin-4-ylidene) thiosemicarbazide and its hydrochloride: evidence for the existence of a stable imine tautomer in the solid state of 4-aminoquinoline free bases, an anomalous case in nitrogen heterocycles | |
| Aydin et al. | Synthesis, characterization, and crystal structure of bis [4-(3′-benzoyl) thiocarbamidophenyl] ether | |
| Masllorens et al. | Synthesis and characterization of novel homo-and heterobimetallic palladium (0) and platinum (0) complexes of olefinic bismacrocyclic ligands. |